OK, I figured it out . . . for those that are also having issues and to keep it simple:
1. Choose your font from Font Squirrel and download the font kit (i.e. "Times-fontfacekit.zip"
2. Extract the font folder from the .zip and upload this folder to your "fonts" folder within your template.
3. Check the stylesheet.css for that font and find the font-family name (i.e. "TimesRegular").
4. Rename the folder you uploaded to the font-family name i.e. change "Times-fontfacekit" to "TimesRegular".
5. In your template configuration > fonts, use the "TimesRegular" name in both font name and font directory input boxes.
6. If you use different fonts for the base and header, change the font name appropriately in the name and directory input boxes.
7. It should work now!